A highly diastereoselective spiro-cyclopropanation reaction of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides has been developed via a base-induced annulation. This efficient and simple protocol features simple operations, mild conditions and excellent functional...

3 41-Aryl-3-(2-ethoxycarbonylphenyl)carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aryl isocyanates, reacted with primary diamines in 1:1 and 2:1 molar ratio under mild conditions to give selectively the regioisomers 3-aminoalkyl-2-arylaminoquinazolin-4(3H)-ones 3 and 3,3'-disubstituted bis-2-arylaminoquinazolin-4(3H)-ones 4 in good yields, respectively. To fully characterize the regioselectivity of aza-Wittig reactions of 1-aryl-3-(2-ethoxycarbonylphenyl)carbo-diimides with primary diamines, crystals of 4e were obtained, and its structure was determined by X-ray crystallography.

Key indicators: single-crystal X-ray study; T = 292 K; mean (C-C) = 0.003 Å; disorder in main residue; R factor = 0.053; wR factor = 0.157; data-to-parameter ratio = 18.2.

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Key indicatorsSingle-crystal X-ray study T = 292 K Mean (C-C) = 0.007 Å R factor = 0.060 wR factor = 0.145 Data-to-parameter ratio = 16.4For details of how these key indicators were automatically derived from the article, see